Haloalkanes and arenes

can you give me the mechanism of this reaction
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133 Replies
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iTeachChem
iTeachChem3mo ago
in one case you have a strong base and an alcohol (ie making it a very strong base - RO-) and in the other it is just NaOH and water. What do you think would happen in the two cases? Do you recall from SN1/SN2 reactions?
Varun_Arora
Varun_Arora3mo ago
No description
Varun_Arora
Varun_Arora3mo ago
@iTeachChem I guess this should work
iTeachChem
iTeachChem3mo ago
dont you need heat for elimination?
Varun_Arora
Varun_Arora3mo ago
We don’t need it per say It’s an accessory that enhances the reaction I’d say that Mostly depends upon the kind of reagent you have The yield won’t be great here as we are not forming a particularly stable alkene but the question seems to expect that we know “elimination” vs “substitution”
iTeachChem
iTeachChem3mo ago
mujhe laga only bulky bases would make e2 happen
Varun_Arora
Varun_Arora3mo ago
Naah it's not like that Any base jiske conjugate acid ka pka is significantly high Alcohols jaise aren't really very acidic The conjugates of them tend to act as bases because of that pka values they have
iTeachChem
iTeachChem3mo ago
That is fine, i was talking about NaOH wala scene :D
Varun_Arora
Varun_Arora3mo ago
Ulti reaction jyada favourable hai
iTeachChem
iTeachChem3mo ago
RO- is clear
Varun_Arora
Varun_Arora3mo ago
NaOH vaale case me to SN2 hi hoga 'cause OH- is a strong enough nucleophile But not as good of a base as RO- Yeah it can act as a base sometimes (Maybe minor product elimination bhi milega but it won't be much) But mostly H20 se Kam acidic species ke conjugates They tend to perform elimination in water (solution is ofc aqueous here 'cause you don't find "neat" NaOH at most places lol) Ahmm I guess I’ve made a mistake And by looking how confident I was….. lol @iTeachChem really sorry 😭
iTeachChem
iTeachChem3mo ago
bro i am oc noob, i keep checking sites haha its all good
iTeachChem
iTeachChem3mo ago
James Ashenhurst
Master Organic Chemistry
Deciding SN1/SN2/E1/E2 (2) - The Nucleophile/Base
Deciding SN1/SN2/E1/E2, Part 2: The Nucleophile/Base. Once we've analyzed the substrate, the next step is to analyze the nucleophile base. Let's dig in.
iTeachChem
iTeachChem3mo ago
these two i checked to be sure
Varun_Arora
Varun_Arora3mo ago
I just checked ethanol and methanol ka pka I just checked this thing And remembered Williamson synthesis 😭 Primary carbon pe there is no stabilisation of that alkene That’s why it forms the SN2 product Heyy @Prasan sorry for this Sending you the correct thing wait
Varun_Arora
Varun_Arora3mo ago
No description
Varun_Arora
Varun_Arora3mo ago
Ngl I’m making a lot of mistakes these days @iTeachChem 😭 It’s sleep deprivation fr Last night @hardcoreisdead was asking me a few questions….. I missed a carbon while counting in many of them 😭
Varun_Arora
Varun_Arora3mo ago
Btw https://youtu.be/3mxIzuN8gqQ?si=D3QjNW9dBkiDf1Qi you can use this for reference @Prasan
Organic Chemistry with Victor
YouTube
SN1 SN2 E1 E2 Predictive Model || How to determine the mechanism
In this video I'll show you a quick method how to determine the mechanism when it can be either SN1, SN2, E1, or E2. 00:00 Introduction and Review of the Mechanisms 04:25 Predictive Model Overview 05:25 Reagents' Nature 09:34 Predictive Model Details 📝 Download the Organic Chemistry Study Notes 📝 https://www.organicchemistrytutor.com/sho...
Sephrina
Sephrina3mo ago
lmfao i made him forget sn1 and sn2 too
Varun_Arora
Varun_Arora3mo ago
To whom lmao? The guy who asked?
Sephrina
Sephrina3mo ago
u
Varun_Arora
Varun_Arora3mo ago
Lol I just need sleep at this point
Sephrina
Sephrina3mo ago
if only i could be fixed ths way :sweaty:
Varun_Arora
Varun_Arora3mo ago
I guess I can When I'm not sleepy I don't usually say shit like that 😭
iTeachChem
iTeachChem3mo ago
you good bhai?
Prasan
PrasanOP3mo ago
@Varun_Arora the answer given is according to your rxn that you sent first in which you made ethene.
Varun_Arora
Varun_Arora3mo ago
See if it's given that way.... It's wrong I've explained you the reasoning above They just wanted to know ki you know the difference between a base and a nucleophile But they took a bad example to test that If this ever shows up on the exam, then follow this It would not be wrong I can guarantee
Prasan
PrasanOP3mo ago
alright
Varun_Arora
Varun_Arora3mo ago
If it does to unki side se issue hai They gotta fix it as you challenge and stuff
Prasan
PrasanOP3mo ago
bhai bhot problem ha oc mei kya btaun
Varun_Arora
Varun_Arora3mo ago
Ngl these people make questions while they are half asleep
Prasan
PrasanOP3mo ago
fr tho
Varun_Arora
Varun_Arora3mo ago
Mera first solution was a pure result of me being sleep deprived 💀🙏
Prasan
PrasanOP3mo ago
jee mains vale aise kaam kar rahe hain
Varun_Arora
Varun_Arora3mo ago
Literally williamson synthesis works like so good in the lab Vo bhool gaya mai neend me 😭 Mains advance dono bhai
Prasan
PrasanOP3mo ago
adv mei bhi hua aisa?
Varun_Arora
Varun_Arora3mo ago
Advanced me still it kinda gets a bit more logical
Sephrina
Sephrina3mo ago
in basic NTA
Varun_Arora
Varun_Arora3mo ago
They do make shitty questions yes Har saal aata hai wurtz ka ek question jo lab me nahi karwata koi reaction Multiple products me se choose karwate hain jo bante bhi nahi hain lab me
Prasan
PrasanOP3mo ago
yar please give some tips on oc. i just finished haloaklanes and haloarenes and the quesns are very tricky for me rn
Varun_Arora
Varun_Arora3mo ago
Just want to you to eliminate the other options and pick out a possibility jo hoti bhi nahi hai favoured actual conditions me They would be for now I'll just say hang on
Sephrina
Sephrina3mo ago
same same qwestion
Varun_Arora
Varun_Arora3mo ago
Aldehydes and Ketones Vo chapter acche se karna Don't stress out too much about anything before that 'cause if you study this chapter "logically" You can basically do almost all of 11th-12th OC and even beyond tbh
Prasan
PrasanOP3mo ago
okayy and i had another quesn in ngp
Varun_Arora
Varun_Arora3mo ago
Hmm
Prasan
PrasanOP3mo ago
ill just send the quesn wait
Varun_Arora
Varun_Arora3mo ago
Hmm batayo kya question hai Sure Abhi neend me nahi hun utna hopefully sahi ho 😭
Prasan
PrasanOP3mo ago
No description
Sephrina
Sephrina3mo ago
isme to cynide additon hoga na in the halogen replacement
Varun_Arora
Varun_Arora3mo ago
Alcoholic* Notice
Prasan
PrasanOP3mo ago
isme ngp hoga
Sephrina
Sephrina3mo ago
aaa
Prasan
PrasanOP3mo ago
bas kaise hoga isme dikkat
Varun_Arora
Varun_Arora3mo ago
Are you sure
Prasan
PrasanOP3mo ago
yes
Varun_Arora
Varun_Arora3mo ago
Let me see for a moment ruko
Sephrina
Sephrina3mo ago
alkyl cynaide hi to banega
Varun_Arora
Varun_Arora3mo ago
Nahi Alcoholic hai Cyanide would form HCN Which is a weak acid To deprotonate nahi hoga jyada After it's protonated by the alcohol
Sephrina
Sephrina3mo ago
....
Sephrina
Sephrina3mo ago
No description
Varun_Arora
Varun_Arora3mo ago
Bhai how is this..... Let me check pka Wait a sec
Sephrina
Sephrina3mo ago
i remember this very nicely cuz maine kafi ques kiye hai isme
Varun_Arora
Varun_Arora3mo ago
No description
Varun_Arora
Varun_Arora3mo ago
I don't know this seems weird for some reason
Sephrina
Sephrina3mo ago
..it does but mechanism banao
Varun_Arora
Varun_Arora3mo ago
'cause I've always heard of HCN being a weaker acid than alcohols Doing that wait
Sephrina
Sephrina3mo ago
yup ill try too even if it gets protonated where will the proton come from?
Prasan
PrasanOP3mo ago
sahi baat ha
Varun_Arora
Varun_Arora3mo ago
The alcohol Acidic enough to protonate a stronger base Cyanides are weird I gotta understand them today I guess Kayi baar base ki tarah behave karte hain Kayi baar nahi Ohkay There's this new thing I got to know RO- is better solvated in alcohols than cyanides are 'cause oxygen is a better hydrogen bond acceptor (you might not studied hydrogen bonding with respect to this acceptor-donor definition) (I can elaborate on this if you guys want) (maine khud ye pehli baar tab padha tha when I was solving someone's doubt around this only) (we literally rediscovered hydrogen bonding that day lmao)
Sephrina
Sephrina3mo ago
yes pwease
Varun_Arora
Varun_Arora3mo ago
See
Sephrina
Sephrina3mo ago
damn
Varun_Arora
Varun_Arora3mo ago
What's there in a hydrogen bond One molecule provides a proton That can be taken up by an electronegative atom
Sephrina
Sephrina3mo ago
i mean its like a partial bond isnt it?
Varun_Arora
Varun_Arora3mo ago
Yeah it is
Sephrina
Sephrina3mo ago
thts why we use dotted line
Varun_Arora
Varun_Arora3mo ago
The bond kind of oscillates between the too Yeah exactly
Sephrina
Sephrina3mo ago
how so?
Varun_Arora
Varun_Arora3mo ago
It's like dono jagah hai thoda thoda Like one has an actual bond But that bond becomes a bit weaker
Sephrina
Sephrina3mo ago
ahh ok
Varun_Arora
Varun_Arora3mo ago
Some of the electron density "shifts" And intermolecular attraction improves
Sephrina
Sephrina3mo ago
hn it will
Varun_Arora
Varun_Arora3mo ago
(of course if the h bonding is intermolecular) So now
Sephrina
Sephrina3mo ago
hn
Varun_Arora
Varun_Arora3mo ago
The atom that provides you with a proton It should be electropositive enough to not cry when another atom takes up the proton The donor And the other one should be electronegative enough to take it The acceptor
Sephrina
Sephrina3mo ago
so like when a molecule with enough electropositivity and having H bonding during a rxn can give proton easier? than other parts of the molecule
Varun_Arora
Varun_Arora3mo ago
It will affect the reactivity of the acceptor Kyunki hydrogen bonding is usually a "solvent effect" Solvent interact karke makes it difficult for the reacting species
Sephrina
Sephrina3mo ago
hn
Varun_Arora
Varun_Arora3mo ago
To go and attack the species it intends to So hamare case me There is only one donor Alcohol But there are two acceptors Cyanide and Alkoxide
Sephrina
Sephrina3mo ago
so the h bonding area can either make reaction very east or bhery hard?
Varun_Arora
Varun_Arora3mo ago
YES EXACTLY
Sephrina
Sephrina3mo ago
ok ok got it now
Varun_Arora
Varun_Arora3mo ago
Now in this case
Varun_Arora
Varun_Arora3mo ago
No description
Sephrina
Sephrina3mo ago
par ye sab humari ncert mata ke queestion me hoga use?
Varun_Arora
Varun_Arora3mo ago
Isse correct answer aayega actual vala Ncert mata me kuch chizon ki explanation hai nshi Vahan use ho sakta hai
Sephrina
Sephrina3mo ago
okey
Varun_Arora
Varun_Arora3mo ago
This equilibrium will be favoured forward Bohot saara RO- hoga solution me
Sephrina
Sephrina3mo ago
but is wale question me yeh nhi use hoga na? cuz nta
Varun_Arora
Varun_Arora3mo ago
I'm still weirded out ngl Abhi trying to figure out kya hoga CN- will substitute That's sure Uske aage dekhta hun
Sephrina
Sephrina3mo ago
hn
Varun_Arora
Varun_Arora3mo ago
On how the "NGP" thing goes on here
Fusion
Fusion3mo ago
kuch? bhai organic ki ncert ke 30% reactions ka mech nhi hai plus kaafi cheezein ye trick i.e. markovnikoff se batate hain
Varun_Arora
Varun_Arora3mo ago
I mean... Yeah
Sephrina
Sephrina3mo ago
lmfao
Varun_Arora
Varun_Arora3mo ago
I honestly think organic is written in the worst way possible in NCERT
Fusion
Fusion3mo ago
ncert sucks.
Varun_Arora
Varun_Arora3mo ago
They've not done it well at all I only love how they've written physical chemistry
Fusion
Fusion3mo ago
physical sucks as well
Sephrina
Sephrina3mo ago
is question me to SN1 hoga kya?
Varun_Arora
Varun_Arora3mo ago
Naah
Sephrina
Sephrina3mo ago
so much
Varun_Arora
Varun_Arora3mo ago
SN2 Carbon pe hai negative
Sephrina
Sephrina3mo ago
kyu?
Varun_Arora
Varun_Arora3mo ago
Strong enough nucleophile Solvent se mechanism decide nahi hoti "enhance" hoti hai Agar SN1 ho rahi hai To polar Protic me better hogi But agar hoi SN2 rahi hai
Sephrina
Sephrina3mo ago
i need revision for sure
Varun_Arora
Varun_Arora3mo ago
Dw I need it too I'm in a worse condition I guess
Sephrina
Sephrina3mo ago
chalo phy time i will go
Varun_Arora
Varun_Arora3mo ago
Yeah sure do
Sephrina
Sephrina3mo ago
fry hoke aungi organic karne
Varun_Arora
Varun_Arora3mo ago
Will ping you Jab ho gaya I'll get done with this
Sephrina
Sephrina3mo ago
hn please
Prasan
PrasanOP3mo ago
ouh bhai physics hi to ha jo logical ha, chemistry mei to kbhi kbhi lagta kuch bhi chalraha ha
Fusion
Fusion3mo ago
Kuch bhi nahi chal rha bhai
Varun_Arora
Varun_Arora3mo ago
Ye bhi logical hai bhai Taught very wrongly tbh
Fusion
Fusion3mo ago
Agreed
Prasan
PrasanOP3mo ago
haan yar youtube channel batado koi chem ke liye badhia oc with victor, yehi dekhlu?
Varun_Arora
Varun_Arora3mo ago
It’s good Don’t get dependent on it though And tbh jee neet organic me vaise bhi they don’t expect much logic Vo expect karte hain ki tum yaad kar lo Use your logics well yes But the exam will throw you with weird questions and some weird solution where all of it fails So yeah try to understand as much as you can Ask teachers Ask people here
Prasan
PrasanOP3mo ago
alright thanks bro +solved @Varun_Arora @Sephrina
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